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Search results; Over 1,000 homes in Madison

Top guest favourite
Farm stay in Madison
Madison Nature Getaway
1 bedroom, 2 beds, 1 private bathroom
19–24 Jul
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4.98 out of 5 average rating, 225 reviews
Guest favourite
Home in Woolford
Gorgeous Waterfront, Beach, Pool, Pets- 7 Bd /5ba
7 bedrooms, 13 beds, 5 bathrooms
29 Aug – 3 Sept
4.98 out of 5 average rating, 87 reviews
Guest favourite
Home in Woolford
"Endless Summer" on the Chesapeake!
4 bedrooms, 7 beds, 2.5 bathrooms
17–22 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Place to stay in Cambridge
Wye Three Oaks
2 bedrooms, 4 beds, 1 bathroom
25–30 Jul
4.96 out of 5 average rating, 96 reviews
Top guest favourite
Home in Madison
Madison Bay Club House
3 bedrooms, 7 beds, 2.5 bathrooms
27 Aug – 1 Sept
5.0 out of 5 average rating, 50 reviews
Top guest favourite
Home in Woolford
Starboard on McKeil Point, w/heated pool & hot tub
6 bedrooms, 11 beds, 4.5 bathrooms
5–10 Sept
4.99 out of 5 average rating, 141 reviews
Top guest favourite
Home in Cambridge
Relaxing Retreat on the Hudson
5 bedrooms, 5 beds, 2 bathrooms
24–29 Aug
4.96 out of 5 average rating, 73 reviews
Top guest favourite
Home in Cambridge
Sunset Breezes - quiet waterfront retreat
3 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
4.99 out of 5 average rating, 218 reviews
Top guest favourite
Home in Woolford
Newly Renovated Modern 3 bed 2 bath Water Front
3 bedrooms, 3 beds, 2 bathrooms
19–24 Jul
5.0 out of 5 average rating, 246 reviews
Top guest favourite
Home in Cambridge
Chesapeake Sunset Cottage
2 bedrooms, 2 queen beds, 2 bathrooms
31 Aug – 5 Sept
4.97 out of 5 average rating, 104 reviews
Guest favourite
Cabin in Lusby
Waterfront Log Cabin: Deep Work & Nature Retreat
3 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
5.0 out of 5 average rating, 5 reviews
Home in Cambridge
Family and Pet-Friendly, Waterfront with Pier
4 bedrooms, 5 beds, 1.5 bathrooms
27 Sept – 2 Oct
Top guest favourite
Home in Cambridge
Serene getaway with great waterfront views!
3 bedrooms, 5 beds, 2.5 bathrooms
23–28 Jul
5.0 out of 5 average rating, 41 reviews
Top guest favourite
Home in Cambridge
Modern Chesapeake Waterfront - Heated Pool - Dock
5 bedrooms, 8 beds, 3.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Cambridge
280 Acre Waterfront Estate With Dock and Pool
5 bedrooms, 10 beds, 6 bathrooms
1–8 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Woolford
Waterfront Getaway with Dock
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.94 out of 5 average rating, 187 reviews
Guest favourite
Home in Cambridge
Blue Water Farm - Chesapeake Waterfront Estate!
7 bedrooms, 11 beds, 5.5 bathrooms
21–26 Aug
5.0 out of 5 average rating, 19 reviews
Superhost
Home in Woolford
Eastern Shore Waterfront-Pier, Kayaks, FirePit
2 bedrooms, 4 beds, 1 bathroom
26–31 Jul
Guest favourite
Home in Cambridge
Choptank Riverside Retreat
3 bedrooms, 4 beds, 2 bathrooms
3–8 Aug
4.92 out of 5 average rating, 12 reviews